Vacation rentals in North Canaan, CT

Best vacation rentals and Airbnb offers in North Canaan, CT

A Meadow House

B & B, North Canaan

A Meadow House is a b & b in North Canaan, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

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About A Meadow House

A Meadow House is a b & b in North Canaan, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $974.

From$122/night

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Cozy Cabin in the Berkshires

Cabin, North Canaan

Cozy Cabin in the Berkshires is a cabin in North Canaan, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Cabin in the Berkshires

Cozy Cabin in the Berkshires is a cabin in North Canaan, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,761.

From$252/night

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5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires!

Holiday Home, North Canaan

5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires! is a holiday home in North Canaan, with pet-friendly space and kitchen access. This stay gives travelers a…

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About 5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires!

5 Minutes from The Appalachian Trail and Mount Washington. In the Berkshires! is a holiday home in North Canaan, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,805.

From$258/night

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Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires

Cottage, North Canaan

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires is a cottage in North Canaan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires

Peaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires is a cottage in North Canaan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,994.

From$285/night

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Vacation rentals with a pool in North Canaan, CT

Add a pool to the search when you want an easy place to cool off between outings.

Lovely vacation home on secluded hillside with views and heated pool

Holiday Home, North Canaan

Lovely vacation home on secluded hillside with views and heated pool is a holiday home in North Canaan, with pool access. This stay gives travelers a comfortable base for exploring the…

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About Lovely vacation home on secluded hillside with views and heated pool

Lovely vacation home on secluded hillside with views and heated pool is a holiday home in North Canaan, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,779.

From$683/night

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Fantastic 2-bedroom house with AC in quaint Hillsdale.

Holiday Home, North Canaan

Fantastic 2-bedroom house with AC in quaint Hillsdale. is a holiday home in North Canaan, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable…

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About Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale. is a holiday home in North Canaan, with pet-friendly space, pool access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,135.

From$734/night

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Rustic House w/ Heating + Pool

Holiday Home, North Canaan

Rustic House w/ Heating + Pool is a holiday home in North Canaan, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Rustic House w/ Heating + Pool

Rustic House w/ Heating + Pool is a holiday home in North Canaan, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, non smoking, pets::not allowed, pets not allowed, and non smoking::all.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $7,917.

From$1,131/night

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Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer!

Holiday Home, North Canaan

Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer! is a holiday home in North Canaan, with pet-friendly space and pool access. This stay gives travelers a comfortable base for…

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About Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer!

Hot tub, Sauna, Game Room, Fireplaces + Heated Pool in Summer! is a holiday home in North Canaan, with pet-friendly space and pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $13,605.

From$1,944/night

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Vacation rentals with parking in North Canaan, CT

Find vacation rentals that make arriving by car easier.

Charming Berkshire Bungalow: Deck, Firepit, Stargazing

Holiday Home, North Canaan

Charming Berkshire Bungalow: Deck, Firepit, Stargazing is a holiday home in North Canaan, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the…

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About Charming Berkshire Bungalow: Deck, Firepit, Stargazing

Charming Berkshire Bungalow: Deck, Firepit, Stargazing is a holiday home in North Canaan, with outdoor space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, parking, free parking, fireplace, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,311.

From$330/night

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Nature Retreat Near Prospect Lake

Holiday Home, North Canaan

Nature Retreat Near Prospect Lake is a holiday home in North Canaan, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Nature Retreat Near Prospect Lake

Nature Retreat Near Prospect Lake is a holiday home in North Canaan, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,697.

From$385/night

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Steepletop: Nature Lover’s Paradise w/Rec Room

Holiday Home, North Canaan

Steepletop: Nature Lover’s Paradise w/Rec Room is a holiday home in North Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Steepletop: Nature Lover’s Paradise w/Rec Room

Steepletop: Nature Lover’s Paradise w/Rec Room is a holiday home in North Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,790.

From$399/night

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Hilltop Escape with Views & Hot Tub

Holiday Home, North Canaan

Hilltop Escape with Views & Hot Tub is a holiday home in North Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Hilltop Escape with Views & Hot Tub

Hilltop Escape with Views & Hot Tub is a holiday home in North Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,132.

From$447/night

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Pet-friendly vacation rentals in North Canaan, CT

Bring your pet along with stays that welcome four-legged travelers.

Luxurious & Modern 3 BR 1.5 Bath Log Cabin

Cabin, North Canaan

Luxurious & Modern 3 BR 1.5 Bath Log Cabin is a cabin in North Canaan, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Luxurious & Modern 3 BR 1.5 Bath Log Cabin

Luxurious & Modern 3 BR 1.5 Bath Log Cabin is a cabin in North Canaan, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,224.

From$318/night

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Best of the Berkshires + Hot Tub by Evergreen Home

Holiday Home, North Canaan

Best of the Berkshires + Hot Tub by Evergreen Home is a holiday home in North Canaan, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Best of the Berkshires + Hot Tub by Evergreen Home

Best of the Berkshires + Hot Tub by Evergreen Home is a holiday home in North Canaan, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,949.

From$421/night

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Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Holiday Home, North Canaan

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions is a holiday home in North Canaan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a…

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About Beautiful Berkshire Home - Enjoy summer, fall & winter attractions

Beautiful Berkshire Home - Enjoy summer, fall & winter attractions is a holiday home in North Canaan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,007.

From$572/night

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Romantic and Secluded Berkshire's Gem

Cabin, North Canaan

Romantic and Secluded Berkshire's Gem is a cabin in North Canaan, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Romantic and Secluded Berkshire's Gem

Romantic and Secluded Berkshire's Gem is a cabin in North Canaan, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,669.

From$667/night

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Vacation rentals with a kitchen in North Canaan, CT

Compare stays with kitchen access for longer trips and easier meals.

Private Berkshires Getaway Minutes to Ski Butternut

Holiday Home, North Canaan

Private Berkshires Getaway Minutes to Ski Butternut is a holiday home in North Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private Berkshires Getaway Minutes to Ski Butternut

Private Berkshires Getaway Minutes to Ski Butternut is a holiday home in North Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,253.

From$465/night

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Charming Copake Falls House

Holiday Home, North Canaan

Charming Copake Falls House is a holiday home in North Canaan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Charming Copake Falls House

Charming Copake Falls House is a holiday home in North Canaan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,254.

From$465/night

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Catamount, Zip Line, Private Setting, Book Now!

Holiday Home, North Canaan

Catamount, Zip Line, Private Setting, Book Now! is a holiday home in North Canaan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Catamount, Zip Line, Private Setting, Book Now!

Catamount, Zip Line, Private Setting, Book Now! is a holiday home in North Canaan, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,387.

From$484/night

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Pristine 3 Bedroom, Walk-to Gt Barrington Center!

Holiday Home, North Canaan

Pristine 3 Bedroom, Walk-to Gt Barrington Center! is a holiday home in North Canaan, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Pristine 3 Bedroom, Walk-to Gt Barrington Center!

Pristine 3 Bedroom, Walk-to Gt Barrington Center! is a holiday home in North Canaan, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,444.

From$492/night

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Family-friendly vacation rentals in North Canaan, CT

Plan a trip with stays that give families more room to spread out.

Scribe`s Stable | A/C • Screened in Porch • Sleeps 6

Country House, North Canaan

Scribe`s Stable · A/C · Screened in Porch · Sleeps 6 is a country house in North Canaan, with parking and room for a group. This stay gives travelers a comfortable base for exploring the…

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About Scribe`s Stable | A/C • Screened in Porch • Sleeps 6

Scribe`s Stable · A/C · Screened in Porch · Sleeps 6 is a country house in North Canaan, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,006.

From$287/night

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Beautiful Getaway - Right on the Lake-Close to Skiing

Holiday Home, North Canaan

Beautiful Getaway - Right on the Lake-Close to Skiing is a holiday home in North Canaan, with easy beach access and kitchen access. This stay gives travelers a comfortable base for…

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About Beautiful Getaway - Right on the Lake-Close to Skiing

Beautiful Getaway - Right on the Lake-Close to Skiing is a holiday home in North Canaan, with easy beach access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, kids friendly, kids friendly videos or books, and beachfront.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,029.

From$290/night

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Stylish 3 Bedroom Cottage located in a Picturesque Lake community

Cottage, North Canaan

Stylish 3 Bedroom Cottage located in a Picturesque Lake community is a cottage in North Canaan, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Stylish 3 Bedroom Cottage located in a Picturesque Lake community

Stylish 3 Bedroom Cottage located in a Picturesque Lake community is a cottage in North Canaan, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,265.

From$466/night

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Private Woodland Getaway minutes from Ski Butternut

Holiday Home, North Canaan

Private Woodland Getaway minutes from Ski Butternut is a holiday home in North Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private Woodland Getaway minutes from Ski Butternut

Private Woodland Getaway minutes from Ski Butternut is a holiday home in North Canaan, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, kids friendly, kids friendly videos or books, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,753.

From$536/night

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